I’ve thought a lot about what I would say in this entry. How do you get someone who doesn’t listen to you, to listen to you.
How do you admit to yourself that you are not getting through to someone and that they don’t care what you have to say?
It’s like having a 1:1 meeting where the person just says yes, and agrees for 30 minutes and then goes back to doing whatever it was they did before.
I suppose parents have been doing this forever with teenagers, but the workplace is different than the home.
As a CS leader that has joined organizations many time with an existing team in place, this has happened to me quite a bit. It’s very hard to be the new guy when there is a team there already, most of whom do not want a boss, a new boss, or another person who thinks they know more than them talking to them about just about anything.
It’s difficult to navigate, and I’m not sure I could even give the best advice on how to handle this because each company is different, each team is different, each product and manager is different. The goals are different. The scenario is different.
Maybe the team has just been “maintained” for the past 6 months while they find a new leader. Maybe there never was a leader or the person who was there was a weak/ineffective manager and hired poor talent. Or maybe they hired great talent and then quit or got fired. There are an endless number of scenarios here so you can’t plan for all of them.
For me, its about trying to build trust with the team, get quick wins, and really understand what they want to get out of working together. Then its about ensuring each person that reports to you gets that in every interaction.
As a leader you need to deliver at all times, in every interaction, even if you’ve had a shitty day and you don’t want to.
This is B2B SaaS it is not life or death. But that is the responsibility to own when you take up the mantle of leadership. I think that is probably what is the hardest responsibility of being a leader. Ensuring you’re operating at 100% every time when someone needs you. Its being able to always say “yes of course, how I can I help you” after someone or some group of people has called your name or aske “can I ask you something?” 100 times a day. It’s exhausting, but you owe it to them each and every time.
So what do you do when someone won’t listen as you give direction?
There are a number of things I’ve tried.
- Being vulnerable with the IC:
- Share stories, find out what makes them tick, direct the conversations and meetings towards that.
- Try to find out what that person likes and direct the convos there
- Play towards whatever their ambition is
- Show them results, that encourage them to get better.
- If you cannot get the person to engage, or if they are private or anxious, ask more questions, but keep it professional
- Find out their motivations and then keep it very metrics oriented and business-like.
- Manage the person out
- Be direct, ask them why they’re not doing what you’re asking them to do
- Threaten with purpose, in a professional way
- “These are our team and corporate goals, why can’t you hit them? Explain to me why you can’t or won’t do these things?”
- Escalate and loop in HR if you have that
- Ensure you have the support of your leadership team.
There is only so much you can do though, so be easier on yourself. Consider that someone might have something going on outside of work as well, and part of the conversation might be to understand if they need your support.
Here’s a more structured framework per ChatGPT:
1. Pause and Diagnose Before Reacting
- Separate emotion from facts: Don’t react in the moment. Document what was asked, how it was refused, and any undermining behavior.
- Ask yourself:
- Is this defiance about disagreement or disrespect?
- Is the person confused about priorities, overworked, or testing boundaries?
- Are there signs of deeper disengagement or cultural misalignment?
The right approach depends on whether this is a one-off or a pattern.
2. Have a Direct, Private Conversation
- Address it quickly—don’t let it fester.
- Use a calm, fact-based approach:
“I noticed that when I asked for X, it didn’t happen, and afterward, you said Y in front of the team, which undercut the direction we set. Help me understand what’s going on.”
- Give them space to share their perspective. Sometimes it reveals burnout, misunderstanding, or legitimate concerns.
3. Reaffirm Expectations and Accountability
If the behavior was intentional or repeated:
- Restate the non-negotiables:
- Everyone aligns around decisions, even if they disagreed beforehand.
- Open disagreement is welcome, but undermining leadership is not.
- Be explicit about next steps:
- “I expect you to execute on the decisions made. If you disagree, let’s discuss it openly beforehand, not afterward.”
This shows you support healthy debate before decisions, but enforce unity after decisions.
4. Decide on a Path Forward
- If behavior changes: Great—support them, coach them, and move forward.
- If behavior persists: Escalate to formal performance management with HR involvement:
- Document the behavior
- Issue clear improvement expectations and timelines
- Be willing to replace toxic employees if needed
Tolerating repeated undermining sends a dangerous cultural signal to the entire team.
5. Prevent Future Issues
Reinforce cultural values: Respect, accountability, and teamwork should be non-negotiable.
Clarify decision-making processes: RACI models (Responsible, Accountable, Consulted, Informed) help people know their role.
Foster psychological safety for disagreement: People should feel heard before decisions are made.
Robert Statsky 